It is his work in these combination chronicles/post-mortems that led to Shoemaker writing a book on the very subject, entitled, “The Squared Circle: Life, Death, and Professional Wrestling,” released this past October. Less an indictment of the unflattering elements of the business, “Squared Circle” provides an artistic look at the colorful lives of many of wrestling’s departed icons, from The Fabulous Moolah and Andre the Giant, to Bruiser Brody and Macho Man Randy Savage, up to modern-day stars like Eddie Guerrero and Chris Benoit. In his synopses, Shoemaker discusses the cultural impact of each performer, effortlessly observing beneath the surface to tell the reader these stories from a rare perspective: even-handed yet blunt, while also displaying a dry sympathy to their tale.

Shoemaker occasionally interacts with readers on his Twitter, where, despite his dealings with death in the industry, he displays an upbeat and insatiable appetite for all things wrestling.

1. How did a fan and scribe like yourself end up getting the golden ticket to write for Bill Simmons’ Grantland.com?

Before Grantland I was writing a column called ‘Dead Wrestler of the Week’ for Deadspin, so the real question is how I ended up getting the golden ticket to write for Deadspin. I was acquaintances with Tommy Craggs, who runs the site now, but was the number two back then. Whenever something funny would pop up on a wrestling message board that I thought would be good Deadspin fodder, I’d shoot him an email. After he ran with some of them and they got a lot of attention, he asked me to do a regular column, which eventually metastasized into Dead Wrestler of the Week. At that time there wasn’t much in the way of pro wrestling coverage on mainstream sports sites (or mainstream sites in general), so I had a sort of different audience and different sort of exposure than other wrestling writers. Fast forward a couple years, and Craggs was briefly in talks to go to Grantland. That never materialized, but luckily he had already talked to them about bringing me along. I emailed some with Simmons and he was really interested in me covering the current product (as opposed to the strictly nostalgia stuff I was doing for Deadspin), and so I started pitching format ideas and the rest is history.

2. Your moniker of “The Masked Man” instantly resonates with wrestling fans, especially those who remember firsthand the barrage of hooded baddies on television, and in the territories. What made you take on the pen name in your writing endeavors?

Originally I was going to write the Deadspin column with a partner who couldn’t be named, so we joked about using a combined pseudonym. He (or she) never ended up contributing, but Craggs and I loved the moniker too much to let it go. It turned out to be a great thing for me, career-wise. From the first column, people in the comments were trying to guess who I really was, as if I were an established writer secretly slumming it as a wrestling writer instead of the truth, which was that I was a nobody.

3. What period of wrestling would you say is the zenith of your fanhood?

Judging by the amount of memorabilia in my mom’s house, it’s the Attitude Era. But going by passion (at least what I remember of it), it has to be either that WrestleMania 3 Hulkamania heyday or the past few years. Fanhood’s a two-way street — the product has to be good and you have to be invested, you have to give yourself over to it. One of the cool things about writing for Grantland is giving myself over to wrestling again like I did organically when I was a kid. I watch every week, and I don’t look for excuses to miss Raw. And twitter is great too for real-time engagement — you have to pay attention. Nothing will probably mean as much as Ted DiBiase paying Earl Hebner to have plastic surgery to screw Hogan, but today is pretty great. And with twitter and message boards and Hulu and YouTube, being a wrestling fan now is easier and more rewarding than ever.

4. This past summer, you did a series for Grantland on the greatest ‘shoots’ in professional wrestling, bringing up Bruiser Brody’s lack of cooperation with Lex Luger, “The Spider Lady” incident, among others. Why are shoots such a fascinating endeavor to fans who invest in characters and concocted stories?

The single most interesting thing in pro wrestling in the modern era is the interplay between the real and the fake. Nothing else is even close. Wrestlers wink at the audience in promos, workrate is based on how real it looks and how physically demanding it is, pushes only matter in the context of backstage rumors. Shoots are the epitome of this, those amazing moments when the fabric of unreality tears and something real comes through. Ridiculous as the wrestling world can be, it’s actually really rare that we get a terrible on-screen blooper, or for that matter, anything WrestleCrap worthy (Vince Russo’s oeuvre notwithstanding). But it’s a live-action product, and so the exceptions are preserved for posterity, and they’re amazing not just as bloopers but because they’re a commentary on the entire enterprise. They’re also cool stories to tell, because most of them are notorious, but like everything else in the wrestling world, there are multiple competing accounts of every fact. Getting to the bottom of them is a journey in itself.

5. In your writing work, you keep up with the pulse of the wrestling scene with strong regularity, and write about it at length. Is it difficult to do, seeing as mainstream wrestling skews younger, and that detail-happy viewers like yourself are bound to be besieged with plot holes and inconsistencies?

If I get criticism for anything, it’s that I give WWE too much credit, and I’ll accept that — like I said earlier, I gave myself over to it when I decided to take the job. I’ve been incredibly critical of WWE, and I’ll continue to be, but I approach it from a point where I’m trying to like it. Sometimes I have to try really hard. But the notion of writing twice a month just shitting all over the product didn’t appeal to me at all. And there’s total legitimacy in people who do that — there are guys I see that I agree with 95% of what they write, but I just wouldn’t do it that way.

All of which is to say that I usually write from a point of view that everything is intentional, the occasional shoot aside. It’s more fun for me as an intellectual experiment to tie together the continuity as if it’s deliberate than poking holes in it. I’ll leave that to the experts like you guys.

6. Your book, The Squared Circle: Life, Death, and Professional Wrestling, is a straightforward, no-excuses account of a number of wrestling tragedies, while also providing a certain wistful look back at the colorful careers that these men and women had. As a fan, was there one particular death in the business that made you question why you even watch?

A lot of the writing started with the Deadspin column, obviously, and the first time the tragedy really hit home was Chris Kanyon. I think he was the first guy I wrote about who had just died, and he was relatively young and not too far removed from being on WWE television. The crazy thing was I was never a big Kanyon fan, but to deal with such sadness in real time — well, it takes a toll. Writing the book was a great experience and I wouldn’t do it differently, but it involved in wallowing in death to a pretty unhealthy degree. Thank god my publisher wanted a broader history and I got to delve into the business in a more general way too or it might have been too much. The last chapter is about Benoit and Guerrero, and it was the last thing I wrote. That chapter was just grueling. Normally I love writing the big-concept parts and have to muddle through the straightforward career recap parts, but in that chapter I looked forward to the boring parts just to avoid the argument, because the argument was so tragic.

7. When writing the book, taking on all of the ugliness of the business at once, how did it affect your view of wrestling as a fan? Did all of the morbid reality further jade you, or have you found a detached balance between journalist and fan?

Honestly, most of the tragic deaths were things I knew about, even the ones I hadn’t written about before. The bulk of the learning process in writing the book was way less depressing. All of the figures I profile in the book are dead (save the Ultimate Warrior, but that’s kind of the point) but a lot of them died long ago and not necessarily sadly. The broader historical aspects of the book were amazing to research and piece together. It’s a cliche, but the real life is often more interesting than the in-ring storylines are. That stuff made me love the industry even more than I had before, and that balanced out the misery of the more tragic aspects. But even from the beginning, I didn’t dwell on death, despite the rubric. What mattered to me was what these wrestlers represented, and why we fans cared about them. Their characters and what they meant were bigger than life and death. The distance between that and their very human deaths is incredibly interesting. Morbid, sure, but there’s a lot more to it than that.

8. In one lengthy aside in your book, you detail the history of race in wrestling, from crowd segregation in the South, to broad stereotypes accepted as functional gimmicks. When you see acts these days like Los Matadores or Hunico (prior to adopting Sin Cara’s duds), do you believe these low-hanging tropes will always exist in wrestling?

I think that broad tropes will always exist, yes. Wrestling at its base is about conveying your character to the guy in the 50th row, so crass simplicity is an intrinsic part of the form. But race isn’t inherently an issue. As America continues to drift towards a less racially divided status quo, the wrestling world will follow suit. Wrestling’s always reflected our culture, for better or for worse. (And it’s not specific to wrestling — Hunico was dressed just like a million Latino characters on TV and in the movies.) In that context, the race section is as much a cultural commentary as it is a wrestling one, though it’s hard to read that piece and not see it as pretty damning to the wrestling industry over the years. But there’s good that comes with the bad — guys like Junkyard Dog and Sputnik Monroe broke down racial barriers in the South in ways that wouldn’t have been imaginable without pro wrestling.

9. In your chapter on the life, career, and death of Curt Hennig, you state at the end, “We are the Mr. Perfect generation,” citing that his persona was an inadvertent usher of modern-day, never-in-the-wrong, know-it-all snarkiness, particularly in the internet age. Is it fair to say we’re more of a ‘schadenfreude’ generation, in that we’d sooner pick apart the misfortunes and blunders of others, while masking the make-up of our own lives?

Absolutely. I alluded to it earlier when I was talking about other wrestling writing, but it’s a larger problem of the internet in general. It’s too easy to be negative. It comes too naturally with the anonymity that online writing provides — I mean that literally, of course, but that’s less of a problem. I of all people wouldn’t fault anyone their pen names. It’s the bulletproof feeling that comes with writing consequences-free into the ether. And it’s cumulative. You go on any message board — not just wrestling — and you’ll see a hundred people complain about a hundred totally different things and yet they come away thinking they all agree, and that affects the way people view next time, because they approach it expecting the worst. That’s sad to me because every point of view is legitimate, but if the overall effect is you enjoy things less, then the only thing you’re getting out of this amazing new technological movement is dissatisfaction. /End old man grumbling

10. You get to write for a website run by the well-known Bill Simmons, have published a book, and just recently interviewed perhaps WWE’s most currently-revered star in Daniel Bryan. On your wrestling and journalism bucket list, what’s the item with the heaviest underline?

Great question. There are a few pieces I want to do soon that aren’t bucket list subjects but just cool stories that sort of transcend wrestling that I’m excited to get out to a bigger audience. I interviewed Triple H last summer, which was amazing. There are only a handful of people who would come close to that — Vince, Hogan, Flair, JR, and Heyman but he’s already said a lot. I’d love to get Punk the day he retires. I’m almost more interested in talking to much smaller names, though, because with the legends it’s basically impossible to penetrate the wall of ego and unreality. They’ve been living fictional lives for decades, so it’s really not that surprising. It’s just not terribly interesting.

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Justin Henry is WrestleCrap's inquiring newsman, thirsting for knowledge always. He enjoys the art of satire, as you'll find in many of his works here at WrestleCrap. Drop him a line on Facebook (http://www.facebook.com/notoriousjrh) and Twitter (http://www.twitter.com/jrhwriting)